Esters of polyvalent alcohols



eric acid anhydride and 45 proportionflof benzylchloride,

Patented Jan. 19, 1932 MARTIN BOLL'MANN, 0'1

PANY, INCL, OF

BERLIN, GERMANY, NEW YORK, N. Y.,

assreiuon rowm'rnnor CHEMICAL 001 c A COBPORATTON OF NEW YORK ESTEBS or POLYVALENT AnconoLs No Drawing. Application filed March 20, 1929, Seri The present invention relates to the new compounds of the general formula 5 where R means an alkyl group, R means a radicle comprising an aryl or aralkyl group and R" means an acyl group containing at 1 least three carbon atoms. A

These derivatives of polyvalent alcohols, for instance 0 1.2-dihydroxyethane, 1 3- dihydroxypropane, 1.2.3-trihydroxypropane are useful as perfumes and flavorings, as t ey are generally characterized by a fruity sweet odor of high permanence. 1 The new compounds may troducing into the hydroxyl be made by ingroups of polyvalent alcohols, in any order, arylor aralkyl the phenyl, amethylphenyl or the benzyl-group ,2 and acyl-groups containing at least three carbon atoms, for example, the propionyl, butyryl, isobutyryl, benzoyl, cinnamyl-group, or by causing the corresponding esters of halogen alcohols to react with phenolates.

The following examples illustrate the process:

E wample 1.-1 molecular proportion of 1- groups, for example,

phenoxy-Q-hydroxyethane 1s heated to boiling with 0.6 molecular proportion of isoval- 0.13 molecular proortion of sodium isovaleriate for 8 hours in a reflux apparatus. After cooling the product is washed until neutral and fractionate in a vacuum. 7

E wample 2.1 molecular-proportion of 1- para-methylphenoxy-2-hydroxyethane and 1 molecular proportion of isobutyric acid are heated together for 8 hourswhile thetemperature gradually rises to 205 0., whereby 11berated water is distilled{ The product is washed untilneutral and'fractionated in a vacuum.

E wample 3. 1 molecular proportion of 1- butyryloxy-2-hydroxyethane, molecular 0.5- molecular a1'No..3 48,663, and-in Germanylovemberfi, 19.28. V

proportion of calcium lecularproportions of water are m1x'ed, and the mixture, oiled for 8 hours in a refluxapparatus. After cooling, the product washed until neutral and fractionat ddn a vacuum. Y

E mample l s-rEquimolecnlar' proportions of 1-butyry1oxy 2-chlorethane and tassium phenolate are heated together for 6 hours in a reflux apparatus. After cooling,

- the product is washed until neutral and fractionated in avacuum.

Among other compounds which can be made according to the invention aresr I 1-phenoxy-2 propionyloxy-ethane;' I,

Oo-oHfcHFo-co41ra-om l x g a colorless liquid, 'D =1.085, 13p 121? C; Herbaceous odor, resemblinghya- C'lllth. f

a colorless I liduid, D' :==1.06(), .Bp. C. Fruity, sweet odor. g 1-pl1enoxy 2 -isobutyryloxy-ethan, V

a colorless liquid, n1,- =1,05s, B a m:

Gt Fruity, sweet odor.

V1-phenoxy-2-isovaleryloxy5ethane,'

05 0am "BF- m a colorless liquid, D lee-136C. Fruity, sweet odor. a y r eee y:2 be Y 9 rP e- O eneres O e m resem es am-1;

r eolorless crystals,meltingpointfia C. Feeble" 50 carbonate'and m l-ortl1o-methylphenyloxy-2-isobutyryloxyat 15 0., hich boils at 124-125 0 1-phenoxy-2-cinnamyloxy-ethane,

colorless crystals, melting point 64 C. Feeble herbaceous odor.

l-para methylphenoxy 2 isobutyryloxyetl1ane, V

a colorless liquid, D =1,035, Bp.

C. Fruity, sweet odor.

ethane,

a colorless liquid, -D ='1,037, Bp.

128130 C. Fruity, herbaceous odor. 1benzyloxy-2-isobutyryloXy-ethane,

a colorless liquid, D =1.034l, Bp. 5 134-137 C. Fruity, sweet odor,

1-pheno2ry-3-1sobutyryloxy-propane,

a colorless liquid, D =1.023, Bp.

' I claim 1. The new compounds of the general formula R-O-R where R means an alkyl group, R means an aryl or an aralkyl group, and R meansan acyl group containing at least three carbon atoms.

Fruity, sweet odor.

2. The new compounds of the general for mula R,-O-CH means an aryl or means an acyl carbon atoms.

3. The new formula v aryl-O-R R means an alkyl group means an acyl group containing at least three carbon atoms.

g R, where R an aralkyl group, and R" group containing at least three butyryloxy-ethane having the formula being colorless liquid whose density is 1.035 under a pressure of 3 mm. of mercury and which has a fruity, sweet odor.

he new 1-phenoxy-3-isobutyryloxypropane having the formula.

being a colorless liquid whose density is 1.023 at 15 (1., which boils at 138141 C. under a pressure of 3 mm. of mercury and which has a fruity, sweet odor.

n testimony whereof, I afiix my MARTIN BOLL signature.

MANN. 

